A rocky shoreline with a boat, a house, and a forest in the background.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Bailey Island holiday homes

A wooden deck with outdoor seating and string lights.

1. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is £279
includes taxes & fees
5 Oct - 6 Oct
Full sized home
A cozy living room with a wooden ceiling, a sofa, a table, and a sliding glass door leading to a balcony.

2. Mid Coast Getaway w/ water views

Mid Coast Getaway w/ water views
West Point
9.2 out of 10, Wonderful, (10 reviews)
"The location and views from the cottage are quintessential coastal Maine. Small community with lobster pound and Maine Oyster Company across the street. John is a welcoming host and eager to make sure you enjoy your stay. The cottage is great for 2 people, equipped with the basics and has a great deck to enjoy the views. Planning to return next year. Great spot!"
United States
Rebecca
The price is £154
includes taxes & fees
1 Oct - 2 Oct
Mid Coast Getaway w/ water views
A spacious room with a wooden floor, a dining area with chairs and a table, a sofa, a TV, and a balcony with a view of the sea.

3. 2 bedroom w/ expansive water views

2 bedroom w/ expansive water views
West Point
10.0 out of 10, Exceptional, (5 reviews)
"Place was clean, beautiful and the photos do not do it justice. The perfect get away vacation from the rat race."
United States
Gregory M.
The price is £197
includes taxes & fees
30 Sept - 1 Oct
2 bedroom w/ expansive water views
A lakeside property with a deck, picnic table, and barbecue grill.

4. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is £283
includes taxes & fees
3 Oct - 4 Oct
Camp Forever cottage
A deck with white railings overlooking a body of water, boats, and a forested shoreline.

5. Captains Watch: A Coastal Escape

Captains Watch: A Coastal Escape
West Point
The price is £144
includes taxes & fees
30 Sept - 1 Oct
Captains Watch: A Coastal Escape
A covered porch with a view of a lake and trees.

6. Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (10 reviews)
"Lovely location "
United States
Michelle S.
The price is £310
includes taxes & fees
5 Oct - 6 Oct
Mere Point Sunrise Views at Eastern Shore!
A lush garden with a hammock, a variety of flowers, and a lake in the background.

7. Classic New England Waterfront House Big Lawn Beautiful Sunrise

Classic New England Waterfront House Big Lawn Beautiful Sunrise
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! "
United States
Ashma B.
The price is £1,352
includes taxes & fees
13 Oct - 14 Oct
Classic New England Waterfront House Big Lawn Beautiful Sunrise
A wooden deck with a view of a lake, surrounded by trees and shrubs.

8. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (73 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is £356
includes taxes & fees
30 Sept - 1 Oct
Centerview cottage
A spacious bedroom with a large bed, a rocking chair, and a view of a balcony with a white railing.

9. Fantastic Waterfront Views

Fantastic Waterfront Views
West Point
9.6 out of 10, Exceptional, (20 reviews)
"The location and views were incredible. Quiet and relaxing spot."
United States
Vanessa W.
The price is £138
includes taxes & fees
7 Oct - 8 Oct
Fantastic Waterfront Views
A living room with a sofa, armchair, wooden coffee table, and a potted plant.

10. Fully Updated Airy Historic Home in South Freeport

Fully Updated Airy Historic Home in South Freeport
Freeport
The price is £388
includes taxes & fees
1 Oct - 2 Oct
Fully Updated Airy Historic Home in South Freeport
A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

11. Quiet Spot in lovely Freeport neighborhood

Quiet Spot in lovely Freeport neighborhood
Freeport
The price is £279
includes taxes & fees
11 Oct - 12 Oct
Quiet Spot in lovely Freeport neighborhood
A treehouse with a wooden staircase and a small building with a colorful mural.

12. Perfect stopover, getaway, base to explore the area, or to simply stay in town.

Perfect stopover, getaway, base to explore the area, or to simply stay in town.
Bath
8.0 out of 10, Very good, (31 reviews)
"A charming, quiet, and clean room with separate bathroom close to everything downtown. Felt a bit like staying at my grandparent’s house in a good way - it’s very homey. Dmitri is very nice and communication was thorough and easy!"
United States
Esther
The price is £145
includes taxes & fees
1 Oct - 2 Oct
Perfect stopover, getaway, base to explore the area, or to simply stay in town.
A wooden staircase with a wooden railing, surrounded by green foliage.

13. 1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!

1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
Bath
8.2 out of 10, Very good, (21 reviews)
"Cute but aging small space, Near attractions"
United States
michael
The price is £147
includes taxes & fees
5 Oct - 6 Oct
1BR Apt. Walk to everything, Large yard. Treehouse. Sun porch. Fall in Maine!
A room with a sliding glass door leading to an outdoor deck with Adirondack chairs and a table.

14. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
10.0 out of 10, Exceptional, (11 reviews)
The price is £839
includes taxes & fees
7 Oct - 8 Oct
Three bedroom in United States of America, Freeport
A rocking chair and a small table with a decorative plate, both placed on a wooden deck in front of a red building with a white door.

15. 2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.

2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
Bath
9.0 out of 10, Wonderful, (28 reviews)
"Clean, walkable to town, nice backyard to sit and talk."
United States
Kathleen
The price is £209
includes taxes & fees
1 Oct - 2 Oct
2BR Apt. Authenticic value, Walk to everything, Large yard, Treehouse. No fees.
A modern kitchen with a large island, dark cabinetry, and a view of a lake.

16. The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury

The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
Harpswell
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property, well equipped, lots of amenities, plenty of space for our large group."
United States
Edwin M.
The price is £1,704
includes taxes & fees
5 Oct - 6 Oct
The Harpswell House-1.6 Acres Waterfront, SunRise, Big Yards, Classic & Luxury
A cozy room with wooden flooring, wicker furniture, and a white brick wall.

17. Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard

Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
Brunswick
10.0 out of 10, Exceptional, (5 reviews)
"Great location"
United States
Ashley W.
The price is £557
includes taxes & fees
30 Sept - 1 Oct
Brunswick 3BR Bungalow By Bowdoin With Fenced-In Backyard
A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

18. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is £447
includes taxes & fees
1 Oct - 2 Oct
Lush Coastal Downtown Home - Beaches & Shopping
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

19. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is £294
includes taxes & fees
29 Oct - 30 Oct
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

20. Luxe 5 Bed/ 3 Bath with Game Room & AC

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is £707
includes taxes & fees
30 Sept - 1 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bailey Island Hotel Reviews

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Friendly staff. Basic hotel but clean and comfortable."
Mack 1-night trip
Posted less than an hour ago
Tru by Hilton Portland Airport Area

Find out more about Bailey Island

Bailey Island Holiday Homes information

Number of reviews
418
Accommodation
614 Holiday Homes
Lowest Price
£138
Highest Price
£1,704